Over the course of his journey with JetBlue's All-You-Can-Jet pass, Eric Barkin crisscrossed the country—10 flights to 8 cities in 30 days. We've adapted his travelogue here, but you can read the full version on our blog at http://sn.im/dcrmblog-aycj.

I was expecting to be on hold forever. I was buying it on the second day of the offer, when a lot of the major news outlets had started picking it up. I didn’t even have to wait the slimmest second, though. I was patched through to an agent immediately and was done with the whole purchase on the inside of 10 minutes.

In a lot of ways, what followed was one of the most fun parts of my adventure across America. The days when I was plotting out my route, there was an intense feeling of freedom and possibility. Really, I could pretty much go anywhere inside of the continental United States whenever I wanted to. I spent hours in front of JetBlue’s map figuring it all out. As I stared to figure it all out, I must confess, I actually started to get a little disappointed. There would be so many places I wouldn’t be going.

2. Booking the Flights

Location: New York

Again, I had almost no wait time getting to an agent. Each flight (there were around 10 total) had to be input manually and separately by the contact center agent. On top of that, for each one I also had to be confirmed, assigned a seat, and then booked. The limitations of JetBlue’s then Navitaire-based system were on full display. The whole process took much longer than it should have. Furthermore, it was clear that JetBlue’s protocols had been designed for making a few flights at a time—probably the norm—but the company didn’t seem to make proper provisions for the massive, simultaneous bookings that the All-You-Can-Jet pass clearly required.

I’m sure these frustrations expressed themselves with other flyers. When I asked the agent on the line if my itinerary of 10 to 12 flights was one of the crazier ones she had done so far, she said, “Actually, it’s pretty typical.”

3. Trouble in the Contact Center

Location: Rochester, N.Y.; New York; and Ft. Lauderdale, Fla.

I had to change my plans almost as quickly as I made them due to some unforeseen conflicts. I dialed up JetBlue and switched the order of my flights around. The call was easy enough, but proved to be problematic. Because each flight had to be handled separately, the agent who handled my call seemed to have forgotten to cancel my old bookings as she made my new ones. This meant I was double booked.

I didn’t realize this until I got a notice from JetBlue saying that I had missed a flight and would be slapped with a $100 fee. I called JetBlue right away and for the first and only time in my phone interactions with them, was placed on hold for five to 10 minutes. When I got an agent there was a lot of uphill wrangling and explaining that I hadn’t missed any flight, and that the problem was with the booking on the company’s end. There was a lot more of me being placed on hold to check the fine print of the terms, to get authorization from managers, etc., but eventually the airline very nicely waived the fee and fixed my schedule.

In that whole exchange there was a real CRM lesson, though. When I first made the call, I was furious that I was being charged for something I didn’t do, and then resented all the hoops I had to jump through to fix it. However, the contact center agent was very courteous and professional throughout. When she got the fee waived, I was so thankful that I ended up being more pleased with JetBlue for the way it handled a screw up than I would have been if it hadn’t messed up at all.

That is to say, I now had confidence in their ability to fix unforeseen problems and was willing to take chances with them.

4. My Fellow Traveler

Location: Washington

It wasn’t until my fourth flight out of D.C. and into Chicago that I actually met my first, fellow All-You-Can-Jetters. On the other flights the crew had asked who was on the pass, and for us to raise our hands. There were never more than a small handful on any flight and none of them were ever near me. However, on this occasion there was one right next to me. She was a diplomat for the State Department. She was actually using her pass to go back and forth between D.C., her home on the West Coast, and different parts of the world. When she had to book an international flight, she would check fares out of various airports around the U.S. and then use JetBlue to ferry her to the cheapest one.

I asked her if that was working out to be cheaper for her. She said, “Not yet. But soon.”

5. Oh, the Places You Can’t Go

Location: Chicago; Iowa City, Iowa; and Middle America at Large

If you live in or want to go to the Midwest, don’t ask JetBlue for a hand. The only place they’ll take you is Chicago. From the Windy City, I rented a car and had to do a lot of driving to see and write from the “heartland.” The same would have been true for the Old Southwest, had I actually made it. The middle of the country is a big black void on JetBlue’s map. Consequently, part of making this trip work for me was a willingness to drive at extra expense.

6. California, I Love You So

Location: Los Angeles and San Francisco

Majestic mountains, glittering beaches—and the kind of traffic you could really grow old in. I had such a good time in California that I kept changing my plans around to stay longer and longer. I still changed my plans three days in advance, but I switched things around multiple times—one of the immense benefits of the pass’s generous terms. In a lot of ways, the ability to change things around is one of the only things that made it worthwhile. Without the potential for spontaneity it delivered, the pass would have lost much of its value.

7. One Extra Flight

Location: West Palm Beach, Fla.

Making my way back east from California, through Boston and then New York, explicitly to take all my dirty laundry from my apartment to my parents’ place in Florida, I found myself wanting to spend more time than the pass would allow with my family. Tired of traveling and in need of mom-made meals, I booked one extra flight at my own expense back to New York from Florida. This was something I had been considering all along, and something I imagine JetBlue made some real money from—people flying back home at the end of their trip outside the bounds of All-You-Can-Jet.